title: Iron-catalyzed ring-opening azidation and allylation of O-heterocycles.
abstract: We have established the first catalytic C-C and C-N bond formation reactions of O-heterocycles (e.g., tetrahydrofuran, phthalane, and lactone derivatives) using iron trichloride as a catalyst in the presence of TMSN3 or allylsilanes accompanied by the ring opening of O-heterocycles. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from the 2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.
authors.affiliation: Laboratory of Organic Chemistry, Gifu Pharmaceutical University , 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan, Laboratory of Pharmaceutical Physical Chemistry, Gifu Pharmaceutical University , 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan, and Organic Chemistry, Dortmund University of Technology , Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany.
authors.forename: Yoshinari
authors.initials: Y
authors.lastname: Sawama
authors.forename: Kyoshiro
authors.initials: K
authors.lastname: Shibata
authors.forename: Yuka
authors.initials: Y
authors.lastname: Sawama
authors.forename: Masato
authors.initials: M
authors.lastname: Takubo
authors.forename: Yasunari
authors.initials: Y
authors.lastname: Monguchi
authors.forename: Norbert
authors.initials: N
authors.lastname: Krause
authors.forename: Hironao
authors.initials: H
authors.lastname: Sajiki
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000438:Alcohols; D000498:Allyl Compounds; D001386:Azides; D002264:Carboxylic Acids; D002712:Chlorides; D005290:Ferric Compounds; D006571:Heterocyclic Compounds; C024555:ferric chloride